As Monty spends his remaining time as a free man putting his affairs in order, the film takes note of some striking images of New York following Sept. 11. The opening credits show Manhattan skyscrapers from extreme angles, alongside monumental shafts of light, and we gradually realize we're seeing the 9-11 memorial spotlights.
In a later scene, Monty's best friends Jacob (Philip Seymour Hoffman) and Slaughtery (Barry Pepper) discuss his prospects for survival while in prison. The most compelling thing about their conversation isn't what they're saying, but what we see through the picture window behind them: the Ground Zero site itself. Shot at night from far above, it's a remarkable thing to see on the big screen, with bulldozers that seem to be gently cleaning the sacred ground, like morticians respectfully preparing a body.
25th Hour also makes occasional references to Osama bin Laden, but all of the Sept. 11 material has only tenuous, symbolic connections to Monty's story. Lee may be saying that Monty's conviction and upcoming jail term is doing to him what the attack on the World Trade Center did to New York and the rest of the nation. Instead, it's like getting constant reminders that the plot of 25th Hour is trivial and overwrought in the big scheme of things.
Monty's "to-do" list includes meeting with the Russian mobsters he used to work for, as well as visiting his anguished father (Brian Cox), who runs a bar and grill for firemen, providing more 9-11 references. He spends some tense, quiet moments with his Puerto Rican girlfriend Naturelle (Rosario Dawson), even though, against his better judgment, he wonders if she betrayed him to the DEA. And Jacob and Slaughtery take him for a night on the town that's like the world's most depressing bachelor party.
Norton's bearing as Monty conveys a little of the slick hustler he no doubt used to be, although now he's cloaked in defeat. We get little glimmers of Monty's reined-in rage and despair, which occasionally slip the leash. Alone in a restaurant restroom, he looks in a mirror and lets fly with an aria of insult, snapping, "Fuck you!" to everyone he can think of, including the Bush administration, Islamic terrorists and all of New York's ethnic groups. It's like Lee's paying homage to the scene in Do the Right Thing when the characters took turns hurling racial epithets at the camera.
Lee can't resist injecting edgy confrontations wherever he finds them, even though the film mostly has a mournful tone. A subplot has Jacob, a prep school teacher, trying to control his lust for a student (Anna Paquin), the kind of sluttishly-dressed jailbait who seems unconsciously devoted to destroying the careers of her teachers. While Paquin's scenes have sizzle missing from most of the movie, they feel beside the point.
25th Hour does advance a disquieting theme of lusting after younger women. "Who are you trying to be, R. Kelly?" quip Jacob's friends, who advise him to wait until the girl's of legal age, like Monty did with Naturelle. We have a flashback to Monty meeting Naturelle in her schoolgirl's uniform, and while it's one of the film's most relaxed, naturalistic scenes, the subtext is unavoidably creepy.
As a filmmaker Spike Lee has had trouble finding the right place for his passions since Malcolm X. By far his best movie since then was the Civil Rights documentary 4 Little Girls, while 25th Hour has an unjustified feeling of emergency comparable to He Got Game and Summer of Sam. It's like Lee has been trying to tell "little" stories, but they end up too small for his ambitions.